CN117903041A - Water-soluble thickened oil viscosity reducer and preparation method thereof - Google Patents
Water-soluble thickened oil viscosity reducer and preparation method thereof Download PDFInfo
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- CN117903041A CN117903041A CN202211281010.8A CN202211281010A CN117903041A CN 117903041 A CN117903041 A CN 117903041A CN 202211281010 A CN202211281010 A CN 202211281010A CN 117903041 A CN117903041 A CN 117903041A
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- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title claims description 9
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 38
- 238000006243 chemical reaction Methods 0.000 abstract description 35
- 238000003756 stirring Methods 0.000 abstract description 30
- 239000007787 solid Substances 0.000 abstract description 29
- 230000000694 effects Effects 0.000 abstract description 13
- 238000010438 heat treatment Methods 0.000 abstract description 10
- 238000001816 cooling Methods 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 150000002170 ethers Chemical class 0.000 abstract description 2
- 239000012467 final product Substances 0.000 abstract 1
- 238000000643 oven drying Methods 0.000 abstract 1
- 238000010025 steaming Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 75
- 239000010779 crude oil Substances 0.000 description 25
- 230000009467 reduction Effects 0.000 description 19
- 239000002994 raw material Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000002390 rotary evaporation Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000000084 colloidal system Substances 0.000 description 5
- 238000004945 emulsification Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- ROUYUBHVBIKMQO-UHFFFAOYSA-N 1,4-diiodobutane Chemical compound ICCCCI ROUYUBHVBIKMQO-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000013043 chemical agent Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- -1 sodium alkyl sulfate Chemical group 0.000 description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- WXYMNDFVLNUAIA-UHFFFAOYSA-N 1,8-dichlorooctane Chemical compound ClCCCCCCCCCl WXYMNDFVLNUAIA-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GFOBSZSXQKGNMN-UHFFFAOYSA-N 2-[dodecanoyl(methyl)amino]ethanesulfonic acid;sodium Chemical compound [Na].CCCCCCCCCCCC(=O)N(C)CCS(O)(=O)=O GFOBSZSXQKGNMN-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- MYOWBHNETUSQPA-UHFFFAOYSA-N tetradecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCS(O)(=O)=O MYOWBHNETUSQPA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F17—STORING OR DISTRIBUTING GASES OR LIQUIDS
- F17D—PIPE-LINE SYSTEMS; PIPE-LINES
- F17D1/00—Pipe-line systems
- F17D1/08—Pipe-line systems for liquids or viscous products
- F17D1/16—Facilitating the conveyance of liquids or effecting the conveyance of viscous products by modification of their viscosity
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Public Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of tertiary oil recovery, and particularly relates to a water-soluble thick oil viscosity reducer and a synthesis method thereof. The synthesis method comprises the following steps: adding 4-piperidinecarboxylic acid, DMF, dihalide or dihalogenated ether into a four-neck flask, stirring for reaction, maintaining with 1M sodium hydroxide in the reaction process, and cooling to room temperature; adding haloalkane into the four-mouth flask, stirring, preserving heat, reacting, maintaining with sodium hydroxide in the reaction process, and rotary steaming to obtain viscous solid; adding water into the viscous solid, stirring, heating, standing for layering, dissolving the upper layer into water phase, separating out water phase, distilling under reduced pressure to dryness, recrystallizing with solvent, and oven drying to obtain the final product. The viscosity reducer has the characteristics of high activity and low concentration, and can reduce the viscosity of the thickened oil by more than 98 percent under the condition of 300 mg/L.
Description
Technical Field
The invention belongs to the technical field of tertiary oil recovery, relates to a chemical agent used in a thickened oil recovery process, and in particular relates to a water-soluble thickened oil viscosity reducer and a synthesis method thereof.
Background
Thick oil, as the name suggests, is a relatively viscous oil. Refers to high viscosity heavy crude oil with viscosity of more than 50mPa.s under stratum conditions or viscosity of 1000-10000 mPa.s of crude oil is de-aerated at reservoir temperature. Heavy oil resources have a considerable specific gravity in world oil and gas resources. According to statistics, the thickened oil and the super thickened oil account for more than 20% of the crude oil reserves which are ascertained in the world, and along with the continuous reduction of light crude oil easy to be extracted, the thickened oil extraction increasingly attracts attention of various countries. Along with the continuous demand of energy sources for economic development, the thickened oil becomes one of the main battlefields of the future petroleum exploitation in China.
Saturated hydrocarbons, aromatic hydrocarbons, gums, and asphaltenes constitute four components of the crude oil definition family of compositions. The mass percentages of the four components in the crude oil reflect the chemical composition characteristics of the crude oil, and the composition characteristics are closely related to the fluidity of the crude oil. The low saturated hydrocarbon content and high colloidal asphaltene content are the most obvious features of the heavy oil family composition. The type and content of wax in crude oil, the carbon number distribution of monomer hydrocarbon in wax, the content and type of colloid asphaltene and the content of light components have complex influence on the effect of the viscosity reducer.
The main composition of the emulsifying viscosity reducer is a surface active substance, and the surface active agent which can be used as the thick oil emulsifying viscosity reducer mainly comprises nonionic or nonionic-anionic combination type, anionic type, cationic type and compound type. The emulsification viscosity-reducing method is known as a chemical viscosity-reducing method which has an effect on reducing the viscosity of thick oil and has low cost.
CN201210026686.2 discloses a viscosity reducer for crude oil in a thick oil cold-production stratum, which is applied to the treatment of crude oil in the stratum of oil field thick oil cold-production and improves the fluidity of crude oil in the stratum. The weight percentages of the components are as follows: sodium N, N-oleoyl bis taurate: 10.2 to 11.5 percent; sodium lauroyl methyltaurine: 18.6 to 19.0 percent; secondary sodium alkyl sulfate: 15.3 to 15.8 percent; emulsifier OPE-12:3.5 to 4.5 percent; sodium oleate: 0.1 to 0.15 percent; sodium hydroxide: 0.1 to 0.15 percent; the balance of water, and the sum of the weight percentages of the components is hundred percent. The effect is as follows: the viscosity of the thickened oil in the oil layer can be reduced, the fluidity of the thickened oil in the oil layer can be improved, and the problem that the thickened oil of the underground oil layer is difficult to flow into a shaft can be solved. However, when the emulsion is used, an alkaline substance is compounded to achieve a good emulsification and viscosity reduction effect on thick oil, and the addition of the alkaline substance can lead to the expansion of clay on one hand and the potential hazard to the oil extraction process on the other hand, and on the other hand, the later demulsification is difficult, so that extra workload is brought to the crude oil processing.
CN201010152050.3 discloses a water-soluble thick oil viscosity reducer, which belongs to the technical field of viscous crude oil emulsification viscosity reducer, and comprises 0.01-1.0 part by weight of surfactant, 0.01-1.0 part by weight of dispersant and 0.01-0.6 part by weight of demulsifier; the surfactant is a nonionic surfactant selected from OP-10, TX100, span80 and Tween80, the dispersing agent is a water-soluble high polymer material selected from polyacrylamide, polyvinyl alcohol, guar gum and cellulose, and the demulsifier is a polyoxyethylene-polyoxypropylene block copolymer; the invention has good emulsification and viscosity reduction effects; the emulsified crude oil can be automatically demulsified, and the dehydration rate is more than 95%; the viscosity reducer has the advantages of small dosage and low price of the used materials, thereby leading the cost of the viscosity reducer to be low. However, the viscosity reduction effect of the surfactant is limited, and particularly for thick oil with high viscosity, the viscosity reduction rate is difficult to reach 90%, so that the application range is limited.
CN201910795697.9 discloses a water-soluble hyperbranched thick oil viscosity-reducing oil-displacing agent and a preparation method thereof, wherein the viscosity-reducing oil-displacing agent is a polymer formed by copolymerizing 0.01% -1.0% of functionalized skeleton monomer, 10% -20% of acrylamide, 10% -20% of acrylic acid, 40% -50% of nonionic functional monomer octyl phenol polyoxyethylene ether and 20% -25% of anionic monomer sodium 2-acrylamide tetradecyl sulfonate. The viscosity-reducing oil-displacing agent has strong water-phase tackifying capability and good shearing resistance, and has the functions of controlling the fluidity ratio and expanding the swept volume; meanwhile, the viscosity-reducing oil-displacing agent has strong mixing and emulsifying performances with the thick oil, the common thick oil has an emulsifying and viscosity-reducing rate of more than 80 percent and is easy to break emulsion, and the effects of reducing viscosity and displacing oil with one agent are realized. The viscosity reduction oil displacement agent prepared by the method has the advantages of wide sources of raw materials, simple and convenient preparation process and low cost. However, the viscosity reduction rate of 80% is difficult to meet the requirement of viscosity reduction of thick oil, so that practical application is limited.
Disclosure of Invention
The invention provides a water-soluble thick oil viscosity reducer and a preparation method thereof, aiming at the problems existing in the prior art. The water-soluble thick oil viscosity reducer has the advantages of wide sources of synthetic raw materials, simple synthetic process, clean and pollution-free process, and easy obtaining and transportation and preservation of products; meanwhile, the water-soluble thick oil viscosity reducer has the characteristics of high activity and low concentration, and can reduce the viscosity of thick oil by more than 98 percent under the condition of using the concentration of 200 mg/L.
Therefore, in order to achieve the above purpose, in one aspect, the invention discloses a water-soluble thick oil viscosity reducer, wherein the molecular structural formula of the viscosity reducer is as follows:
Wherein:
R is C 3-C8 alkyl or-CH 2CH2OCH2CH2 -;
R 1 is a straight chain alkyl of C 8-C18.
In another aspect, the invention provides a method for preparing a water-soluble thickened oil viscosity reducer, which comprises the following steps: under the condition of substitution reaction, 4-piperidinecarboxylic acid, dihalide or dihalide ether undergoes a first substitution reaction in the presence of DMF; secondly, adding alkyl halide to perform a second substitution reaction, wherein the dihalide or dihalide ether is shown as a structural formula (1); the haloalkane is shown as a structural formula (2);
XRX1 (1)
R1X2 (2)
Wherein R is alkane of C 3-C8 or-CH 2CH2OCH2CH2-,X1 is one of chlorine, bromine and iodine; r 1 is C 8-C18 alkyl, and X 2 is one of chlorine, bromine and iodine.
In a third aspect, the invention provides an application of the water-soluble thickened oil viscosity reducer in thickened oil development and transportation.
The water-soluble thickened oil viscosity reducer belongs to a double-cation double-anion amphoteric surfactant, hydrophilic groups comprise two carboxylic acid groups and two quaternary ammonium salts, and compared with the conventional surfactant with a single hydrophilic lipophilic group, the water-soluble thickened oil viscosity reducer has higher surface activity and lower critical micelle concentration, so that the required dosage is lower. The two long-chain alkyl groups belong to hydrophobic groups, have good oleophylic performance, can be spontaneously inserted into the stacked structure of colloid and asphaltene of the thick oil, break pi-pi conjugation of colloid asphaltene, weaken aggregation force of colloid and asphaltene, easily generate intermolecular interaction with large aromatic ring compounds, long-chain aliphatic hydrocarbons and the like in the thick oil, can more easily strip colloid, asphaltene and the like adsorbed by the oil-water interface of the W/O type thick oil emulsion, and convert the W/O emulsion into O/W emulsion, thereby greatly reducing viscosity of the emulsion.
Compared with the prior art, the invention has the beneficial effects and advantages that:
(1) The water-soluble thick oil viscosity reducer has the advantages of wide sources of synthetic raw materials, simple synthetic process, clean and pollution-free process, and easy obtaining and transportation and preservation of products;
(2) The thick oil viscosity reducer has the characteristics of high activity and low concentration, and can reduce the viscosity of the thick oil by more than 98 percent under the condition of using the concentration of 300 mg/L;
(3) The thick oil viscosity reducer can achieve the ideal effects of emulsification and viscosity reduction in the exploitation and conveying processes and demulsification and oil-water separation in the separation process, has simple demulsification process, reduces the energy consumption while reducing the addition of chemical agents, and thus comprehensively reduces the utilization cost of thick oil resources.
Detailed Description
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
According to a first aspect of the invention, the invention discloses a water-soluble thick oil viscosity reducer, which has the following molecular structural formula:
Wherein:
R is C 3-C8 alkyl or-CH 2CH2OCH2CH2 -, preferably C 4-C6 straight-chain alkyl.
R 1 is C 8-C18 alkyl, preferably C 8-C18 linear alkyl, more preferably C 12-C16 linear alkyl.
According to a second aspect of the invention, the invention discloses a preparation method of a water-soluble thick oil viscosity reducer, which comprises the following steps: under the condition of substitution reaction, 4-piperidinecarboxylic acid, dihalide or dihalide ether undergoes a first substitution reaction in the presence of DMF; secondly, adding alkyl halide to perform a second substitution reaction, wherein the dihalide or dihalide ether is shown as a structural formula (1); the haloalkane is shown as a structural formula (2);
XRX1 (1)
R1X2 (2)
Wherein R is alkane of C 3-C8 or-CH 2CH2OCH2CH2-,X1 is one of chlorine, bromine and iodine; r 1 is C 8-C18 alkyl, and X 2 is one of chlorine, bromine and iodine.
In the present invention, R in formula (1) is a linear alkyl group of C 4-C6.
In the present invention, X 1 in the formula (1) is bromine or iodine.
In the present invention, R 1 in formula (2) is a linear alkyl group of C 8-C18, more preferably a linear alkyl group of C 12-C16.
In the present invention, the X 2 in the formula (2) is bromine or iodine.
In the present invention, the dihalide or dihaloalkane ether is used in an amount of 0.5 to 0.6 mole parts, 1 to 1.2 mole parts, respectively, based on 1 mole part of 4-piperidinecarboxylic acid; more preferably, the dihalide or dihaloether, haloalkane is used in an amount of 0.52 to 0.56 mole parts, 1.05 to 1.1 mole parts, respectively, based on 1 mole part of 4-piperidinecarboxylic acid.
In the present invention, the temperature of the first substitution reaction is 60 to 65 ℃.
In the present invention, the temperature of the second substitution reaction is 110 to 120 ℃.
Preferably, the mass ratio of DMF to 4-piperidinecarboxylic acid is 10-20:1, a step of; more preferably, the mass ratio of DMF to 4-piperidinecarboxylic acid is 10-15:1.
According to a more specific preferred embodiment, the preparation method of the water-soluble thick oil viscosity reducer specifically comprises the following steps:
(1) Adding 4-piperidinecarboxylic acid, DMF, dihalide or dihalogenated ether into a four-neck flask, stirring at 60-65 ℃ for reaction, maintaining pH at 6-8 with 1M sodium hydroxide in the reaction process, and cooling to room temperature;
(2) Adding haloalkane into the four-mouth flask, stirring at 110-120 ℃ for reaction at a temperature of between 6 and 8, and maintaining the pH value during the reaction by using 1M sodium hydroxide, and performing rotary evaporation to obtain a viscous solid;
(3) Adding water into the viscous solid, stirring and heating to 80-90 ℃, standing for layering, dissolving the upper layer which is unreacted raw materials in the water phase, separating the water phase, distilling under reduced pressure to dryness, recrystallizing with a solvent to obtain a solid, and drying at 105-120 ℃ overnight to obtain the water-soluble thick oil viscosity reducer.
Preferably, the stirring reaction time in step (1) is 6 to 12 hours.
Preferably, the stirring and heat preserving reaction time in the step (2) is 24-48h; more preferably, the stirring incubation reaction time is 36-42 hours.
Preferably, the mass ratio of water to 4-piperidinecarboxylic acid in step (3) is 20-30:1, a step of; more preferably, the mass ratio of water to 4-piperidinecarboxylic acid is 20-25:1.
Preferably, the solvent in step (3) is ethyl acetate or n-hexane.
The reaction equation for synthesizing the water-soluble thick oil viscosity reducer is as follows:
in a third aspect, the invention provides an application of the water-soluble thickened oil viscosity reducer in thickened oil development and transportation. There is no particular requirement for the specific application, and the application may be a conventional application manner in the field, and will not be described in detail herein.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.
In addition, the specific features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described further.
Moreover, any combination of the various embodiments of the invention can be made without departing from the spirit of the invention, which should also be considered as disclosed herein.
The invention will be further illustrated with reference to specific examples.
In the present invention, the devices or apparatus used are all conventional devices or apparatus known in the art, and are commercially available.
In the following examples and comparative examples, each reagent used was a chemically pure reagent from commercial sources, unless otherwise specified.
Example 1
(1) 0.1Mol of 4-piperidinecarboxylic acid, 129g of DMF and 0.5mol of 1,3 dichloropropane are added into a four-necked flask, the mixture is stirred at 60 ℃ for reaction for 6 hours, the pH value is maintained at 6-8 by 1M sodium hydroxide in the reaction process, and the mixture is cooled to room temperature;
(2) Adding 1mol of chlorooctane into the four-neck flask, stirring at 110 ℃ and preserving heat for reaction for 24 hours, maintaining pH at 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain a viscous solid;
(3) 258g of water is added into the viscous solid, stirring and heating are carried out to 84 ℃, standing and layering are carried out, the upper layer is unreacted raw materials, the product is dissolved in the water phase, the water phase is separated, reduced pressure distillation is carried out until the water phase is dried, the solvent is used for recrystallization, the solid is obtained, and the product S 1 is obtained after drying at 105 ℃ overnight.
Example 2
(1) 0.1Mol of 4-piperidinecarboxylic acid, 258g of DMF and 0.6mol of 1, 8-dichlorooctane are added into a four-necked flask, stirred and reacted for 12 hours at 65 ℃, and the pH value is maintained to be 6-8 by 1M sodium hydroxide in the reaction process, and cooled to room temperature;
(2) Adding 1.2mol of bromooctadecane into the four-neck flask, stirring at 120 ℃ and preserving heat for reaction for 48 hours, maintaining pH at 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain viscous solid;
(3) 387g of water is added into the viscous solid, stirring and heating are carried out to 88 ℃, standing and layering are carried out, the upper layer is unreacted raw materials, the product is dissolved in the water phase, the water phase is separated, reduced pressure distillation is carried out until the water phase is dried, ethyl acetate is used for recrystallization, the solid is obtained, and the product S 2 is obtained after drying at 115 ℃ overnight.
Example 3
(1) Adding 0.1mol of 4-piperidinecarboxylic acid, 150g of DMF and 0.52mol of 1,4 dibromobutane into a four-necked flask, stirring and reacting for 8 hours at 62 ℃, maintaining the pH value between 6 and 8 by using 1M sodium hydroxide in the reaction process, and cooling to room temperature;
(2) Adding 1.05mol of iodododecane into the four-neck flask, stirring at 115 ℃ and preserving heat for reaction for 30 hours, maintaining the pH value to be 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain a viscous solid;
(3) Adding 300g of water into the viscous solid, stirring and heating to 85 ℃, standing for layering, dissolving the upper layer which is unreacted raw material into a water phase, separating the water phase, distilling under reduced pressure to dryness, recrystallizing with ethyl acetate to obtain a solid, and drying at 120 ℃ overnight to obtain the product S 3.
Example 4
(1) Adding 0.1mol of 4-piperidinecarboxylic acid, 180g of DMF and 0.54mol of 1,4 diiodobutane into a four-necked flask, stirring at 60 ℃ for reaction for 10 hours, maintaining the pH value between 6 and 8 by using 1M sodium hydroxide in the reaction process, and cooling to room temperature;
(2) Adding 1.15mol of bromohexadecane into the four-neck flask, stirring at 112 ℃ and preserving heat for reaction for 36h, maintaining pH at 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain viscous solid;
(3) Adding 310g of water into the viscous solid, stirring and heating to 82 ℃, standing for layering, dissolving the upper layer which is unreacted raw material in the water phase, separating the water phase, distilling to dryness under reduced pressure, recrystallizing with ethyl acetate to obtain a solid, and drying at 110 ℃ overnight to obtain the product S 4.
Example 5
(1) Adding 0.1mol of 4-piperidinecarboxylic acid, 230g of DMF and 0.53mol of 1,4 dibromobutane into a four-necked flask, stirring at 65 ℃ for reaction for 8 hours, maintaining the pH value between 6 and 8 by using 1M sodium hydroxide in the reaction process, and cooling to room temperature;
(2) Adding 1.06mol of bromotetradecane into the four-neck flask, stirring at 118 ℃ and preserving heat for reaction for 30 hours, maintaining pH at 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain viscous solid;
(3) Adding 290g of water into the viscous solid, stirring and heating to 85 ℃, standing for layering, dissolving the upper layer which is unreacted raw material into a water phase, separating the water phase, distilling under reduced pressure to dryness, recrystallizing with cyclohexane to obtain a solid, and drying at 105 ℃ overnight to obtain the product S 5.
Example 6
(1) Adding 0.1mol of 4-piperidinecarboxylic acid, 210g of DMF and 0.52mol of 1,4 diiodobutane into a four-necked flask, stirring and reacting for 8 hours at 64 ℃, maintaining the pH value to be 6-8 by using 1M sodium hydroxide in the reaction process, and cooling to room temperature;
(2) Adding 1.08mol of bromododecane into the four-neck flask, stirring at 113 ℃ and preserving heat for reaction for 30 hours, maintaining the pH value to be 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain a viscous solid;
(3) Adding 330g of water into the viscous solid, stirring and heating to 80 ℃, standing for layering, dissolving the upper layer which is unreacted raw material into a water phase, separating the water phase, distilling under reduced pressure to dryness, recrystallizing with cyclohexane to obtain a solid, and drying at 115 ℃ overnight to obtain the product S 6.
Example 7
(1) 0.1Mol of 4-piperidinecarboxylic acid, 178g of DMF and 0.52mol of 1,4 dibromobutane are added into a four-necked flask, the mixture is stirred and reacted for 10 hours at 63 ℃, and during the reaction, 1M sodium hydroxide is used for maintaining pH value to 6-8, and the mixture is cooled to room temperature;
(2) Adding 1.1mol of bromotetradecane into the four-neck flask, stirring at 115 ℃ and preserving heat for reaction for 36 hours, maintaining pH at 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain viscous solid;
(3) 298g of water is added into the viscous solid, stirring and heating are carried out to 90 ℃, standing and layering are carried out, the upper layer is unreacted raw material, the product is dissolved in the water phase, the water phase is separated, reduced pressure distillation is carried out until the water phase is dried, cyclohexane is used for recrystallization, the solid is obtained, and the product S 7 is obtained after drying at 120 ℃ overnight.
Example 8
(1) Adding 0.1mol of 4-piperidinecarboxylic acid, 215g of DMF and 0.51mol of 1,4 dibromobutane into a four-necked flask, stirring and reacting for 10 hours at 62 ℃, maintaining the pH value to be 6-8 by using 1M sodium hydroxide in the reaction process, and cooling to room temperature;
(2) Adding 1.1mol of bromotetradecane into the four-neck flask, stirring at 115 ℃ and preserving heat for reaction for 40h, maintaining pH at 6-8 by using 1M sodium hydroxide in the reaction process, and performing rotary evaporation to obtain viscous solid;
(3) Adding 325g of water into the viscous solid, stirring and heating to 80 ℃, standing for layering, dissolving the upper layer which is unreacted raw material in the water phase, separating the water phase, distilling under reduced pressure to dryness, recrystallizing with cyclohexane to obtain a solid, and drying at 115 ℃ overnight to obtain the product S 8.
Test example 1 evaluation of Water-soluble thickened oil viscosity reducer
The crude oil used in the experiment is an oil sample of a certain block of a winning oilfield estuary oil extraction plant, and the initial viscosity of the crude oil is 8300 mPa.s at 50 ℃.
The water-soluble thickened oil viscosity reducer S 1、S2、S3、S4、S5、S6、S7、S8 and SL-3 (victory chemical sulfonate) and PPG8000 (polypropylene glycol) were respectively prepared into 300mg/L and 3000mg/L solutions.
Evaluation method refers to Q/SH 10201519-2016 general technical Condition for viscosity-reducing agent for heavy oil
Wherein:
f-viscosity reduction rate,%;
Mu 0 -initial viscosity of crude oil at 50 ℃ mPa.s;
mu-viscosity of crude oil after viscosity reduction, mPa.s.
The test results are shown in Table 1.
TABLE 1 results of viscosity reduction test for oil samples in estuary oil works
As can be seen from table 1: the water-soluble thick oil viscosity reducer S 1-S8 acts on crude oil with the viscosity of 8300 mPa.s, when the using concentration is 200mg/L, the viscosity reduction rate of the crude oil reaches 98% or more, the highest viscosity reduction rate reaches 99.07% (S 8), and the viscosity reduction rates of the common viscosity reducers SL-3 and PPG8000 on the market under the same concentration are 88.19% and 89.28%, respectively, which are obviously lower than the viscosity reducer.
Test example 2 evaluation of Water-soluble thickened oil viscosity-reducing agent
The crude oil used in the experiment is an oil sample of a certain block of a pile-western oil extraction factory of a victory oil field, and the initial viscosity of the crude oil is 15800 mPa.s at 50 ℃.
The test method was the same as in test example 1.
The test results are shown in Table 2.
Table 2 results of viscosity reduction test for oil samples from the western oil extraction plant
As can be seen from table 2: the water-soluble thick oil viscosity reducer S 1-S8 acts on crude oil with the viscosity of 15800 mPa.s, when the using concentration is 200mg/L, the viscosity reduction rate of the crude oil reaches more than 98 percent, the highest viscosity reduction rate reaches 99.06 percent (S 8), and the viscosity reduction rates of the common viscosity reducer SL-3 and PPG8000 on the market under the same concentration are both 0 and are obviously lower than that of the invention.
The water-soluble thick oil viscosity reducer has the advantages of wide raw material sources, simple synthesis process, clean and pollution-free process, and easy product acquisition, transportation and storage; meanwhile, the water-soluble thick oil viscosity reducer has the characteristics of high activity and low concentration, and can reduce the viscosity of thick oil by more than 98 percent under the condition of using the concentration of 200 mg/L. Therefore, the water-soluble thickened oil viscosity reducer has wide application prospect.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.
Claims (16)
1. The preparation method of the water-soluble thick oil viscosity reducer is characterized by comprising the following steps of: under the condition of substitution reaction, 4-piperidinecarboxylic acid, dihalide or dihalide ether undergoes a first substitution reaction in the presence of DMF; secondly, adding alkyl halide to perform a second substitution reaction, wherein the dihalide or dihalide ether is shown as a structural formula (1); the haloalkane is shown as a structural formula (2);
XRX1 (1)
R1X2 (2)
Wherein R is alkane of C 3-C8 or-CH 2CH2OCH2CH2-,X1 is one of chlorine, bromine and iodine; r 1 is C 8-C18 alkyl, and X 2 is one of chlorine, bromine and iodine.
2. The method for preparing a water-soluble thick oil viscosity reducer according to claim 1, wherein R in formula (1) is a linear alkyl group of C 4-C6.
3. The method for preparing a water-soluble thick oil viscosity reducer according to claim 1, wherein X 1 in the formula (1) is bromine or iodine.
4. The method for preparing a water-soluble thick oil viscosity reducer according to claim 1, wherein R 1 in formula (2) is a linear alkyl group of C 8-C18.
5. The method for producing a water-soluble thick oil viscosity reducer according to claim 4, wherein R 1 in the formula (2) is a linear alkyl group of C 12-C16.
6. The method for preparing a water-soluble thick oil viscosity reducer according to claim 1, wherein X 2 in the formula (2) is bromine or iodine.
7. The method for preparing a water-soluble thick oil viscosity reducer according to claim 1, wherein the dihalide or dihaloalkane ether and the haloalkane are used in an amount of 0.5 to 0.6 mol parts and 1 to 1.2 mol parts, respectively, based on 1 mol part of 4-piperidinecarboxylic acid.
8. The method for preparing a water-soluble thick oil viscosity reducer according to claim 7, wherein the dihalide or dihaloalkane ether and the haloalkane are used in an amount of 0.52 to 0.56 mol parts and 1.05 to 1.1 mol parts, respectively, based on 1mol part of 4-piperidinecarboxylic acid.
9. The method for preparing a water-soluble thick oil viscosity reducer according to claim 1, wherein the temperature of the first substitution reaction is 60-65 ℃.
10. The method for preparing a water-soluble thick oil viscosity reducer according to claim 1, wherein the temperature of the second substitution reaction is 110-120 ℃.
11. The preparation method of the water-soluble thick oil viscosity reducer as claimed in claim 1, wherein the mass ratio of DMF to 4-piperidinecarboxylic acid is 10-20:1.
12. The water-soluble thick oil viscosity reducer is characterized by comprising the following molecular structural formula:
Wherein:
R is C 3-C8 alkyl or-CH 2CH2OCH2CH2 -;
R 1 is C 8-C18 alkyl.
13. The water-soluble thickened oil viscosity reducer of claim 12, wherein R is a C 4-C6 linear alkyl group.
14. The water-soluble thickened oil viscosity reducer of claim 12, wherein R 1 is a linear alkyl of C 8-C18.
15. The water-soluble thickened oil viscosity reducer of claim 14, wherein R 1 is a linear alkyl of C 12-C16.
16. Use of the water-soluble thickened oil viscosity reducer according to any one of claims 12 to 15, characterized in that it comprises two aspects: on one hand, the thick oil is developed; and on the other hand, transportation of thick oil.
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